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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap107

Which statements about the Reimer-Tiemann reaction of phenol with $CHCl X_{3}$ and aqueous $NaOH$ are correct?

AThe major product is 4-hydroxybenzaldehyde.
BDichlorocarbene behaves as an electrophile.
CDichlorocarbene is generated from $CHCl X_{3}$ by the action of the base.
DThe species attacked by dichlorocarbene is the phenoxide ion.

Answer: B, C, D

The base abstracts a proton from

CHCl X_{3}

to give

CCl X_{3} X^{-}

, which loses

Cl X^{-}

to give electron-deficient

: CCl X_{2}

. This electrophile attacks the electron-rich phenoxide ion, mainly at the ortho position, so the main product is 2-hydroxybenzaldehyde and the para isomer is the minor one.

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